Organic Letters · 2022 · 16 citations · 57 references
Natural SciencesChemical EngineeringChemistryCatalysisOrganic ChemistryReaction EngineeringSulfur ChemistrySulfur CompoundsCatalyst-free Solvent-free ReactionsFunctional Group ToleranceMild Reaction ConditionsNucleophile ReactivitySolvent Effects On CatalysisSubstrate ScopeSubstrate Scope Expansion
A highly regioselective and catalyst-free sulfonation of allylic alcohols with sulfinyl amides has been realized. Such a mix-and-go procedure provides a convenient approach to synthetically various allylic sulfones under mild reaction conditions. Furthermore, this novel reaction shows ample substrate scope and outstanding functional group tolerance and could also be scaled-up. Meanwhile, it is the first example that sulfinyl amides act as a powerful sulfur nucleophile in the reactions. 1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) as a solvent plays a critical role in allylic sulfonation.
57
Folkert Reck, Fei Zhou, Marc Girardot et al. · Journal of Medicinal Chemistry · 2005 · 326 citations · Full text